Whether or not it’s more blessed to give than to receive, both activities are loaded with lots of potential punishment, particularly if you feel unworthy and/or poor to begin with. If giving is necessary to make you feel worthy, you’ll end up a good-hearted sucker, and if being given to is the only thing preventing you from living in a trailer down by the river, you’ll end up in a black-hearted rage. There’s no need to feel bad about giving or receiving if you feel proud of who you are rather than how well you’re doing. A healthy perspective is the best blessing of all.
–Dr. Lastname

My friends tell me I’m too good to my ex-wife because I always take care of her when she’s in town by giving her a place to stay, feeding her, and tending to her medical needs. Even our kids say she uses everyone, promises everything, and gives back nothing, and, after many years of marriage and an equal number divorced, I know they’re right. I argue back that it’s not smart for me to antagonize her after she’s promised me half the estate she inherited from her dad, but they tell me that she never keeps her promises and she always figures out a way to blow her money on impressing new acquaintances and going on shopping sprees. My goal is to find ways to protect myself and maybe satisfy my friends’ concerns without fighting with my ex- and maybe losing her bequest.

God bless the giving people of the earth—kindergarten teachers, foster parents, 02% of psychiatrists—but I’ve said many times that, no matter how saintly their exterior, the givers’ biggest recipient of generosity is often their immediate feelings.

Let’s face it, giving feels good (partly because it offers peace of mind to the persistently guilty), and that means it’s bad, at least under some circumstances. Giving too much, like any source of good feelings, is dangerous to you and detrimental to the object of your charity.

When you experience the joy of giving, you may be ignoring other personal responsibilities. You may also be enslaving yourself to someone who senses your secret addiction and threatens you with guilt if you don’t do what s/he wants.

Admit it, you’re not taking care of your ex- for her inheritance—you’d probably kill yourself helping her without a cash reward—but now that it’s in the picture, it should be a strong motivator to help less, not more. After all, the big risk here is that you’ll feel bitter if/when she dies and leaves you nothing, either because there’s nothing left or she gave it to her new best friend. Now your bullshit excuse is bullshit in more ways than one.

Meanwhile, your current relationship with her makes her too important, interfering with your ability to find better friendships. Giving can make a compulsive giver very passive, like a waiter (or worse, a manservant).

The opposite of giving isn’t overindulging yourself or aggravating your ex; it’s giving sensibly while considering all your responsibilities. There’s nothing wrong with being kind to your ex, but there’s no need to give unless you think it’s necessary and can afford it, meaning that you’re mindful of your own needs as well.

Ask yourself whether there’s a big trade imbalance between your exports and imports with her. If, when she comes to visit, you think the relationship is unbalanced (meaning she doesn’t put in the time and attention you would expect from a friend), then it’s not good for you.

If your relationship is one-sided, offer a plan for balancing it. Tell her you believe your relationship will work better, in the long run, if you readjust what you and she contribute. She could do this by creating a trust fund to protect your bequest, or making some regular or hourly gift for your services. You’re not critical of her character or past actions, just trying to protect a valued relationship from being spoiled by a destructive imbalance.

If she tells you that she’s entitled to your services and that you’re the one who is ungrateful and un-giving, don’t argue. Simply express your belief in what you think is best for the two of you and insist on your right to agree to disagree.

Don’t throw your friends and other family under the bus to give everything to the one person who doesn’t deserve it. Generosity may give you a buzz, but the cost doesn’t justify any of the rewards, real or fabricated.

STATEMENT:
“I believe it will do nothing but good to equalize the give and take of my relationship with my ex-wife and that it does no good to let fear, guilt or worry about her feelings control what I do. If she refuses to accept what I believe is a reasonable proposal and blames me for destroying our relationship, I will bear the pain of her criticism knowing that we’re both better off putting the manservant into retirement.”

My brother drives me crazy in many ways, but nothing is more infuriating than when he decides to attempt to be generous. He remembers my birthdays and urges me to tell him what I’d like him to get me, but then he doesn’t get around to buying it until my birthday is long past, if at all. The problem is that he has money, I don’t, and if I ask him for something, it’s probably because I can’t afford it myself. Then again, if I really, really need it, I have to get it for myself somehow, which then offends him (and pisses me off). He tells me I’m overly sensitive and paranoid about delays he can’t really help. If I offer him reminders, he acts like I’m nagging him and moves even slower. He’s always been competitive—is he rubbing in his success or just totally oblivious? Should I just stop expecting things from him altogether and get some space?

Poverty and neediness have a way of inspiring resentment and injury. If someone denies you when you’re poor (particularly when you’re not used to being poor), it feels like a personal insult that you should have avoided and should never tolerate again. So it’s entirely possible to feel shafted and shat upon by someone who basically has more good to offer than bad and doesn’t mean to hurt you.

If your feelings take over, you may drive away your pain-in-the-ass brother (assuming he’s not a total jerk), leaving you poorer and madder. It’s like a poverty riot that burns down your own neighborhood.

So put aside your poor-guy feelings and do a business-like evaluation of what your brother has to offer, taking care to value the ways you can count on him (if any) and the things you enjoy about his company. Feeling insulted is not as important as what you think about his ability to be a good friend (sometimes) and to add meaning to your life, simply by being your brother.

While you’re at it, examine whether he does his bait-and-delay to other people. Poverty makes neglect feel personal, but he may be treating you the same way he treats everyone.

If he’s a jerk who usually takes more than he gives (see case above), then you’re right to pull away. It’s sad, but the best you can do.

If, however, he’s not all that bad, then learn to suck up the pain of being a downwardly mobile member of a lower economic class and make the best of your relationship. Not to please him or your family, but for yourself.

STATEMENT:
“I can’t help being poor and having a brother who’s late on delivering stuff I really need, but I won’t let a little pride and/or fury get in the way of a relationship that I value.”